This invention relates to herbicidally active pyrazolesulfonamides having certain heterocycles attached, agriculturally suitable compositions thereof and the method of their use as herbicides and/or plant growth regulants.
In the most common situation, the control of undesired vegetation is desired to permit the growth of useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
European Patent Application (EP-A) No. 95,925 (published Dec. 7, 1983) discloses herbicidal pyrazolesulfonamides in which the group adjacent to the sulfonamide moiety may be selected from H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, OR.sub.16, CO.sub.2 R.sub.23, S(O).sub.n R.sub.24 or SO.sub.2 NR.sub.19 R.sub.20.
EP-A No. 87,780 (published Sept. 7, 1983) claims pyrazolesulfonamides of general formula ##STR1## wherein A is H, C.sub.1 -C.sub.8 alkyl or optionally substituted phenyl;
B and C are independently H, halogen, NO.sub.2, C.sub.1 -C.sub.8 alkyl, CO.sub.2 R, etc.; and PA1 D is H or C.sub.1 -C.sub.8 alkyl. PA1 Q is an unsubstituted or substituted five-membered heterocyclic radical which is bound by way of a carbon atom and which contains 2 or 3 identical or different heteroatoms. PA1 W is O or S; PA1 R is H or CH.sub.3 ; PA1 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl or phenyl optionally substituted by Cl, NO.sub.2, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.2 is H, Cl or CH.sub.3 ; PA1 R.sub.14 is H, C.sub.1 -C.sub.4 alkyl, F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 haloalkylthio, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CO.sub.2 R.sub.17, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl or SO.sub.2 NR.sup.I R.sup.II ; PA1 R.sub.15 and R.sub.16 are independently H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.3 haloalkylthio, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfonyl, F, Cl, Br, CO.sub.2 R.sub.17 or SO.sub.2 NR.sup.I R.sup.II ; PA1 R.sup.I and R.sup.II are independently C.sub.1 -C.sub.3 alkyl; PA1 R.sub.17 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 C.tbd.CH, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 A is ##STR6## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C(O)R.sub.3, ##STR7## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.3 is H or CH.sub.3 ; PA1 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl; PA1 Z is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 Y.sub.2 is H or CH.sub.3 ; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.3 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, OCF.sub.2 H, SCF.sub.2 H, CH.sub.3 or C.sub.2 H.sub.5 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 (1) when X is Cl, Br, F or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2, NH.sub.2 or OCF.sub.2 H; PA1 (2) when X or Y is OCF.sub.2 H, then Z is CH; PA1 (3) when W is S, then R is H, A is A-1, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR8## (4) when the total number of carbon atoms of X and Y is greater than four, then the total amount of carbon atoms of Q and R.sub.2, R.sub.14, R.sub.15 or R.sub.16 is less than or equal to ten; and PA1 (5) when L is L-5, L-6 or L-7, then Q must be bonded to the pyrazole ring nitrogen through a carbon atom. PA1 Q is ##STR9## R.sub.6 and R.sub.9 are independently H or CH.sub.3 ; R.sub.7 is H, CH.sub.3 or Cl; PA1 R.sub.8 is H, SH, CH.sub.3, CH.sub.2 CH.sub.3, S(C.sub.1 -C.sub.4 alkyl), S(C.sub.3 -C.sub.4 alkenyl) optionally substituted with 1 or 2 halogen atoms, S(C.sub.3 -C.sub.4 alkynyl), OCH.sub.3, OCH.sub.2 CH.sub.3, SCF.sub.2 H, CF.sub.3, or S(C.sub.1 -C.sub.3 alkyl) substituted with CN, CO.sub.2 R.sub.4, OR.sub.4 or C(O)CH.sub.3 ; PA1 R.sub.10 and R.sub.11 are independently H, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.12 and R.sub.13 are independently CH.sub.3 or OCH.sub.3 ; PA1 R.sub.18 is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkylthio; and PA1 R.sub.19 is C.sub.1 -C.sub.3 alkyl or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 R.sub.1, R.sub.2 and Q are as previously defined except R.sub.1 is other than H. PA1 Q is Q-1 to Q-24 or Q-29 to Q-40; and PA1 L is L.sub.1 to L.sub.4. PA1 R.sub.1 and R.sub.2 are as previously defined except R.sub.1 is other than H; PA1 Q is Q-7 to Q-13; and PA1 J are appropriate functional groups taught in EP-A No. 83,975 and reference cited therein, to prepare Q groups Q-7 to Q-13. PA1 X' is Br in the 4-position and H in the 5-position; PA1 Q is Q-31 to Q-40; PA1 R.sub.1 is as previously defined with the exception that R.sub.1 does not represent H; and PA1 R.sub.2 is as defined previously. PA1 X" is Br or Cl; and PA1 L is L-1, L-2 or L-4. PA1 X" is Br or Cl; PA1 L is L-1 to L-4; and PA1 R.sub.1 and R.sub.2 are as previously defined. PA1 Q is Q-1 to Q-20; PA1 R.sub.1 and R.sub.2 are as previously defined; and PA1 R.sub.8 is H or alkyl. PA1 Q is Q-1 to Q-4, Q-14 to Q-20, and Q-43. PA1 Q=5, 6, 21-24, 29, 30; PA1 R.sub.1 is as defined except not H; and PA1 R.sub.2 is as previously defined. PA1 Z.sub.1, Z.sub.2 and Z.sub.3, are independently CH or N; and PA1 Q is Q-31 to Q-40. PA1 R.sub.2 is as defined; PA1 R.sub.1 is as defined other than NO.sub.2 on a phenyl ring; and PA1 L is L-1 to L-4. PA1 R.sub.1 and R.sub.2 are as defined; and PA1 J are the appropriate functional groups taught in EP-A No. 83,975 and references cited therein to prepare Q groups Q-1 to Q-20 and Q-43. PA1 R.sub.2 is as defined; PA1 Q is Q-21 to Q-24, and Q-29; and PA1 L is L-1 to L-4. PA1 Q is Q-45, Q-46, Q-47, or Q-48; PA1 L is L-1 to L-4. PA1 R.sub.1, R.sub.18, and R.sub.19 are as previously defined; PA1 L is L-1 to L-4. PA1 Q is Q-25 to Q-28; and PA1 R.sub.1 and R.sub.2 are as defined previously. PA1 Q and R.sub.2 are defined previously; and PA1 L is L-1 to L-4.
South African Patent Application No. 83/3850 published Nov. 28, 1983, discloses herbicidal compounds of general formula ##STR2## wherein R.sub.1 is H or C.sub.1 -C.sub.3 alkyl; and
Unexamined Japanese Patent Application No. 9,013,778 published Jan. 24, 1984 describes herbicidal pyrazolesulfonamides with halo, alkyl and alkoxycarbonyl substituents.
EP-A No. 83,975 (published July 20, 1983) and EP-A No. 85,476 (published Aug. 10, 1983) disclose herbicidal benzenesulfonamides of general formula ##STR3## wherein Q is one of a variety of 5- and 6-membered saturated or unsaturated heterocyclic rings.